1: 1.) potassium hexamethyldisilazide (KHMDS) / 1.) THF, toluene, -78 deg C, 1 h, 2.) THF, toluene, 3 h 2: 24 percent / LiAlH4 / tetrahydrofuran / 4 h / -78 °C 3: 88 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 4: 90 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme

1: 1.) lithium 2,2,6,6-tetramethylpiperidide (LiTMP) / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h 2: 65 percent / LiAlH4 / tetrahydrofuran / 2 h / -40 °C 3: 87 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 4: 66 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme

1: 1.) lithium 2,2,6,6-tetramethylpiperidide (LiTMP) / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h 2: 67 percent / LiAlH4 / tetrahydrofuran / 2 h / -40 °C 3: 89 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 4: 67 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme